O-ethylhydroxylamine hydrochloride → HCID 73769685, compound

HRID 581907Notes

Reaction equation

HRID 581907 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=1)(=O)[CH3:2].Cl.[CH2:26]([O:28][NH2:29])[CH3:27]>C(O)C>[CH2:26]([O:28][N:29]=[C:1]([C:4]1[CH:24]=[CH:23][C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=1)[CH3:2])[CH3:27]

Participants

4

Reactant 2

HCID 76850O-ethylhydroxylamine hydrochlorideHCID 11324445HCID 11324445, compound

Product 1

HCID 73769685HCID 73769685, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

32a from Example 5 (5 g, 15.97 mmol) is suspended in absolute ethanol (50 ml) and heated to 70° C. O-Ethyl hydroxylamine hydrochloride (2.4 g, 24.61 mmol) is added and the mixture is heated to reflux for 1.5 hours. After cooling the solvent is removed by evaporation, and the residue is stirred with aqueous sodium hydroxide (50 ml, 1 M). The crude product is filtered off. Column-chromatographic workup on silica gel using a mixture of ethyl acetate and ethanol (9:1) as the eluent affords pure 33a. Yield: 3.7 g (65%). Mp 105-106° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureAfter cooling the solvent
  4. customis removed by evaporation
  5. filtrationThe crude product is filtered off
  6. additionColumn-chromatographic workup on silica gel using a mixture of ethyl acetate and ethanol (9:1) as the eluent

Sources & evidence

ORD record
ord-694b59b2b09c46b8b850bcfa35cc2fd2
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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